Dean is a Tramp
by TheFireandEarthElf
Summary: Dean and Sam are in trouble with some demons... Again. They need a bit of help. Dean x my original Character. M for graphic sex.


There I was again… My life on the line, the boys lives on the line. When will I ever learn that when The Winchesters blow into town, I should just book it out as fast as I can? I was standing on top of a bar, demons surrounding me. The boys were standing in the back, against the wall, being held there by a demon's telepathic grip. I had to think fast.

"Hey boys, ya wanna know something about Dean Winchester?" I said. Dean's eyes snapped to me and he gave me a confused look. The demons took the bait and all looked at me.

"What is that?" one of the demons snarled at me. My mind raced.

"That he's a tramp" I said, shifting on the bar.

"Hey!" Dean said and the demon tightened his grip.

"You shut up! I want to hear this!" the demon said.

"Yeah," I said then took a deep breath. And I started to sing.

"He's a tramp, but they love him, breaks a new heart, everyday. That Dean's a tramp, they adore him, and I only hope he'll stay that way" I sang in my best Peggy Lee impression. Dean and Sam's eyes widened and they looked almost impressed. The lyrics were perfect for describing Dean Winchester, so perfect I was surprised that I never thought of it before.

"He's a tramp, he's a scoundrel. He's a Rounder, He's a cad" I continued. Dean rolled his eyes. "Deans a tramp, but I love him" Dean's eyes snapped back to me and he gave me a questioning look. I nodded as I kept singing. "Yes, even I have got it pretty bad". I lowered my guard just enough for him to see I was serious.

Right before the end of the song, changing the lyrics but keeping the same tune, began to sing a powerful exorcism spell. It took until the end of the spell to get the demons out of their vessels, but I did it. Dean and Sam nearly fell to the floor when the demon's grip finally let loose. I quickly jumped off the bar and ran to them.

"You guys ok?" I asked. The boys nodded as the panted, catching their breath.

"That was amazing!" Sam smiled and grabbed me, picking me up and hugging me tight. I laughed and swung my feet. My barely 5' stature was no match for his 6' something height. When he put me down, he rustled my hair. Even though I am older than him, he had this habit of treating me like a child, because of my height. I didn't mind, he knew I was just as mature as him, maybe even more. I slowly looked at Dean. He looked like he was at a loss for words, which was surprising. He looked at me fondly and smiled a little.

"Yeah, that was really something" he said, after a moment. "You really saved our hides" he drawled lightly. I smiled. Did he have to look at me with those gorgeous green eyes? I thanked God that I don't blush, otherwise my face would have been beet red at that moment.

I finished off my beer and set the empty bottle on the table, sinking back between Dean and Sam on my couch, watching TV. They told me that they were fine staying at another motel but I wasn't having it. Dean set his empty bottle next to mine and Sam curled up on his side of the couch, falling asleep.

"Sammy, why don't you go to the guest room Michelle setup for you?" Dean said, reaching behind me and nugging Sam, who sleepily nodded and dragged himself upstairs to one of the guest rooms. I smiled at him as he waved goodnight to me. When he was gone, I turned to Dean.

"Want another Beer?" I asked. He nodded and I slipped off the couch. We had all taken showers and I was now in fabric shorts and a black tank top. I opened the fridge then sunk down to a squat to dig around for another beer. I pulled one out and opened it before returning to Dean, pushing it into his hand. He took a greedy guld before setting the now half empty bottle on the table. I looked at me, and I shifted under his green gaze, lowering my hazel eyes back to the TV.

"Michelle?" Dean asked, his voice rough, husky and, damn sexy.

"Yeah?" I replied, pulling my knees up to my chest.

"Did you really mean that? before?" Dean asked. I knew exactly what he meant, but didn't want to say it.

"Mean what?" I asked, playing dumb. I took a lock of my long, blue hair and twirled it around my finger.

"You know what" Dean said, he sounded closer, but I refused to look up. "Do you really love me?" he asked. My heart began to race and I pretended to be fascinated with my hair.

"Um.. " I stalled. Finally, I took a deep breath. "Yes" I whispered. It came out sounding much more weak than I wanted it to. Dean growled and wrapped his arms around me, forcing me to straighten my legs. In one swift move, he placed me on my back on the couch and hovered over me.

"Will you say it again?" He said, bringing his face close to mine. I couldn't breathe. This was happening, it was actually happening. I pinched my leg, wincing at the pain. Dean Winchester was on top of _ME! _Things like never happened to me! Never dorky Michelle! Never.

"Dean" I began then swallowed. "I love you" I said, forcing myself to look into his eyes. His face broke out into a beautiful smile and he dipped his head and took my lips with his. His perfect lips that I have been pining to kiss for almost as long as I have known Dean, were softer than I ever had imagined. He kissed me expertly, gently slipping his tongue in to slide across mine and explore my mouth. He knew just where to bite and suckle as he made his way down my neck and upper chest. His big hands gripped my sides, his fingers playing with the hem of my shirt. My arms wrapped around him and my hands slid up and down his muscular back. His muscles twitched at my touch and I couldn't stop myself from shoving my hands up his shirt and touching his hot skin. His lips broke away from me and whimpered at the loss of contact.

"Your bedroom" he said. I nodded and he lifted me up off the couch and carried me bridal style my room. He lightly kicked the door open and closed, setting me down on my bed. He took a moment to look around my room. I sat, my legs open and biting my lip.

"This room, looks like you" he said with a smirk. I smiled, I was glad to hear it. I loved my room. The collages of pictures on the walls, quotes, weird posters, my old world furniture. Dean's hands went to the hem of his shirt.

"Wait!" I said then scooted to the edge of the bed, where he stood, placing a leg on either side of him and looking up. He smiled at me.

"Let me" I said and stood up on my bed, taking his shirt with me. I threw it across my room and just stared at him, letting my hands roam his perfect body. I kissed his neck, avoiding his lips completely and worked my way down my torso, gently nipping in certain spots, sucking on others. He moaned and wrapped his arms around me.

"Oh Michelle" he breathed and I smiled against his skin. When I got to the edge of his jeans, I heard his breath hitch. The fact that I was soliciting this reaction from Dean made me excited and very horny. I looked up at him as I undid his jeans and hiked them down. His eyes were dilated, the green almost completely gone. I made him fully step out of his jeans and before I could dare touch his boxers, he pushed me down and climbed on top of me again, taking my lips in a rough kiss. His hands found the hem of my shirt again and he pulled it off me then quickly snapped the hook of my bra undone. He impatiently pulled my bra off then sat up for a moment to look at me. I shifted under his intense gaze and instinctively brought my arms up to cover my chest. He placed his hands on my arms and brought them back down.

"Don't hide from me, Michelle. You're beautiful and I want to see you" Dean said and goose bumps rose quickly on my skin. I placed my hand on his cheek and he turned into it and kissed my palm. We shared a loving gaze for a moment before he lowered his head and took one of my nipples into his mouth.

"Ah! Dean" fell from my lips as I knotted my fingers in his hair. He swirled his tongue around it, gently biting and sucking, making it hard. He then moved to the other as his hand slid down my side and fingered the edge of my shorts. I was getting increasingly wetter as time went on, we kissed every inch of each others torso. When he let me roll us so I was laying top of him, I felt incredibly small against his large muscular frame, but very safe. I kissed my way down to his boxers and teasingly mouthed at the erection over the fabric. Dean threw his head back and moaned, placing the heels of his palms on his eyes. I coaxed him to lift his hips up as I pulled his boxers down, freeing his impressively large cock. My heart jumped to my throat and I swallowed. I didn't have the heart to tell him I was virgin, but I have done enough research to know what I was supposed to do. I couldn't deny him any longer. I gently gripped his dick and licked it from base to tip, blowing cool air over the saliva streak I left in my wake. He moaned, apparently that was good. I did that a few more times before swiping my thumb over his slit, which was leaking pre-come and using it as lube to better allow my hand to slide up and down his hot, hard shaft. As I jerked him, my tongue glazed over the head and he hissed. I could tell he was trying hard not to thrust up into my mouth. I soon sunk my mouth over his dick, as far as I could go, sucking and swirling my tongue, using my hands on what I couldn't fit into my mouth. I moved my head up and down and twisted at the tip. Dean's hand fisted in my hair and I let him guide me.

"Damn, that feels good" Dean said, and I moaned, letting the vibrations of my throat work at him even more. I was rewarded with a "shit, Michelle". I kept going, moaning, sucking, licking. I then began to fondle Dean's balls gently and that is when he nearly lost it.

"M- Michelle.. If you keep that up… I'm gonna.. Oh God" Dean babbled and I drew my mouth back with a pop. I kissed my way back up to his lips. I wanted him to cum inside me, while I came on his beautiful cock. I said this to him, in his ear, slow and sexy. He groaned and flipped me over, yanking my shorts and panties down in one pull, flinging them across the room. He kissed down my body and stopped right above the apex between my legs. I sighed and shivered as he studied me. He placed his thumb on my clit and gently rubbed. I sucked in a breath and my head flopped back.

"Dean" I said, a delicate prayer. Soon, I felt lips on me, kissing my soaking wet pussy. He licked my slit, painfully slow before greedily lapping at me. My hips instinctively rolled to create more delicious friction.

"Mmmm, you taste so good" Dean said into my thigh. I moaned and tugged at his hair with one hand and dug the nails of my other, into his shoulder. He knew exactly what to do to get me dripping much more than ever before. He groaned as my nails created welts in his shoulder but the vibrations of his lips drove me wild. Before my orgaasm could hit, he withdrew his mouth from me and kissed his way back up me. I tasted myself on his lips and shivered.

"I know this is your first time" Dean said into my ear. "I'm honored you chose me. If I could go back, I'd choose you too" then he looked at me. I studied his face, he was serious. I smiled and he did as well.

"I-I love you, Michelle" he said. my mouth opened and I tried to say something but no words came. Instead I pulled him into a kiss, hoping it would do my feelings justice. We stayed just kissing for a while until Dean pulled away, panting as much as I was. He then shifted between my legs and looked me in the eyes.

"Are you ready?" he asked. I nodded and bit my lip. I was so wet, he slid in easily. However I did feel a pinch as he did. I winced and he looked at me, apologetically. He stayed still for a moment and just kissed me. It wasn't until I began to roll my hips that he started thrusting into me. Almost immediately, my orgasm began to build. I trembled and moved my hips in time with Dean's. He moaned my name and I moaned his. We were in perfect harmony.

"Fuck me harder!" I nearly screamed. We tried not to get too loud, at least for Sam's sake. Dean slowed his thrusts.

"No, Michelle. I'll make love to you harder" he said as he drove his hips with more force into me. I gasped.

"Talk to me… Love when you speak" I said, my nails digging into his back. He groaned.

"Loved you for so long. Secretly hoped I could come back here. No matter what monster I had to fight, I'd fight anything for you. I'd kill anything for you. I'd kill myself for you" Dean said, he changed his angle slightly and I was slowly falling apart.

"Don't say that, if you died, I don't know what I would do" I said, and it was true.

"Tell me why you love me" he demanded gently. He was kissing my neck, his stubble scratching at me.

"Mmm, I love your loyalty, I love your body, I love your heart, I love your music, I love your humor, I love your eyes, your lips, every inch of you!"

"Fuck! More! Need to hear your voice!" He said, a thrust punctuating each word"

"I love how you make more movie references than me! I love that you know what I am thinking most of the time! I love the way you sing, even though you hate it!" I was gasping and moaning between sentences, I was shattering.

"I love how you sleep! I love your car!" I said and grabbed onto Dean as my orgasm took me.

"Oh God!" he said as I came first. He soon followed and I was a moaning mess as he shot his load into me. He continued thrusting, working us both through our shared orgasm. He collapsed against me when we were spent. a bead of sweat rolling down his temple. I rubbed his back and breathed deep when he pulled out of me. He kissed my neck and snuggled against me, humming in content.

"Was it good? I wanted to make your first time good" Dean said as he looked up at me, his beautiful eyes wide. I planted a soft kiss on his full lips and smiled.

"It was perfect, Dean. I love you" I said and sighed when he layed back on me, head on my chest. I felt like I had the world, with that man's head on my chest.

"You're gonna be sore for a few days" he warned.

"I know" I said, already beginning to feel it.

"Guess I've finally found the Lady to my Tramp" Dean said, stroking my hair. I smiled.

"You are such a sap!" I teased and he smiled.

"Only for you" he said and we soon drifted off to sleep.


End file.
